NPASS Compound

Structure

NPC476311 OpenBabel07101718282D 47 51 0 0 1 0 0 0 0 0999 V2000 1.4778 -3.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1280 -3.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2150 -2.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 -2.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4778 -1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9249 2.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3351 -1.1680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5643 -1.7280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1280 -2.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 -2.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1280 -1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3899 -1.4291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 0.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 -0.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4778 0.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4566 1.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5051 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0769 -0.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 -3.4340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3899 -2.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 -0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9733 2.2392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6527 0.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1690 0.2512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5120 -0.7805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2176 0.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2176 0.3769 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6527 0.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 0.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0214 0.4545 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2176 0.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3051 0.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 3.0869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 -0.7805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9884 0.6856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2176 0.1256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4778 -0.3507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 1.4552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6102 2.2667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.4079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0297 1.6391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0552 3.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5869 3.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7591 0.1256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 36 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 21 2 0 0 0 0 14 24 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 37 1 0 0 0 0 18 26 1 0 0 0 0 22 35 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 24 33 2 0 0 0 0 25 18 1 6 0 0 0 25 31 1 0 0 0 0 25 34 1 0 0 0 0 26 36 1 0 0 0 0 26 38 1 6 0 0 0 27 30 2 0 0 0 0 27 32 1 0 0 0 0 27 33 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 41 1 0 0 0 0 32 42 2 0 0 0 0 33 46 1 0 0 0 0 34 37 1 0 0 0 0 34 43 2 0 0 0 0 35 44 2 0 0 0 0 35 45 1 0 0 0 0 36 47 1 0 0 0 0 37 38 1 6 0 0 0 37 47 1 0 0 0 0 38 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	648.33
Volume:	675.769
LogP:	7.34
LogD:	3.171
LogS:	-3.165
# Rotatable Bonds:	10
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	7.018
Fsp3:	0.553
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.315
MDCK Permeability:	1.3086390026728623e-05
Pgp-inhibitor:	0.4
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.702
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	93.8689193725586%
Volume Distribution (VD):	0.983
Pgp-substrate:	6.775910377502441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.455
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	1.718
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.138
Carcinogencity:	0.343
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.97

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476311

Natural Product ID:	NPC476311
*Common Name:**	QYRPARUSUFWOPG-HBWLMKOJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYRPARUSUFWOPG-HBWLMKOJSA-N
Standard InCHI:	InChI=1S/C38H48O9/c1-19(2)10-9-11-21(5)13-15-23-29(39)24(14-12-20(3)4)33-27(30(23)40)32(42)28-31(41)25-18-26-36(7,8)47-37(34(25)43,38(26,28)46-33)17-16-22(6)35(44)45/h10,12-13,16,25-26,28,31,39-41H,9,11,14-15,17-18H2,1-8H3,(H,44,45)/b21-13+,22-16-/t25-,26-,28?,31?,37-,38-/m0/s1
SMILES:	CC(=CCCC(=CCC1=C(C(=C2C(=C1O)C(=O)C3C(C4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C(=O)O)O)CC=C(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563615
PubChem CID:	45272280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5080.0	nM	PMID[517934]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476311 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1559
0.2-0.3	3227
0.3-0.4	6194
0.4-0.5	10175
0.5-0.6	7799
0.6-0.7	5892
0.7-0.8	7066
0.8-0.85	305
0.85-0.9	46
0.9-0.95	28
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC476210
0.9817	High Similarity	NPC476199
0.9758	High Similarity	NPC473729
0.9639	High Similarity	NPC473607
0.9576	High Similarity	NPC162248
0.9515	High Similarity	NPC476139
0.9515	High Similarity	NPC476152
0.9512	High Similarity	NPC476196
0.9461	High Similarity	NPC233978
0.9451	High Similarity	NPC41598
0.9401	High Similarity	NPC227275
0.9398	High Similarity	NPC476229
0.9387	High Similarity	NPC189689
0.9337	High Similarity	NPC476159
0.9333	High Similarity	NPC158329
0.9333	High Similarity	NPC476146
0.9333	High Similarity	NPC40089
0.9333	High Similarity	NPC476216
0.9333	High Similarity	NPC102810
0.9286	High Similarity	NPC98943
0.9222	High Similarity	NPC169018
0.9222	High Similarity	NPC118128
0.9217	High Similarity	NPC63514
0.9217	High Similarity	NPC47634
0.9217	High Similarity	NPC55422
0.9217	High Similarity	NPC75141
0.9157	High Similarity	NPC223413
0.9141	High Similarity	NPC286422
0.9112	High Similarity	NPC475398
0.9096	High Similarity	NPC476255
0.9096	High Similarity	NPC62444
0.9012	High Similarity	NPC208069
0.8976	High Similarity	NPC131578
0.8941	High Similarity	NPC475080
0.8916	High Similarity	NPC94796
0.8862	High Similarity	NPC476931
0.8851	High Similarity	NPC475656
0.8851	High Similarity	NPC475148
0.8817	High Similarity	NPC193222
0.881	High Similarity	NPC473908
0.8795	High Similarity	NPC43490
0.8795	High Similarity	NPC475107
0.8772	High Similarity	NPC477529
0.8757	High Similarity	NPC476056
0.8743	High Similarity	NPC476929
0.8728	High Similarity	NPC469345
0.8727	High Similarity	NPC164427
0.8721	High Similarity	NPC469393
0.8713	High Similarity	NPC193698
0.8683	High Similarity	NPC472055
0.8675	High Similarity	NPC476930
0.8671	High Similarity	NPC232412
0.8671	High Similarity	NPC98667
0.8671	High Similarity	NPC86809
0.8671	High Similarity	NPC294149
0.8663	High Similarity	NPC473113
0.8655	High Similarity	NPC54903
0.8655	High Similarity	NPC473095
0.8655	High Similarity	NPC286074
0.8655	High Similarity	NPC473096
0.865	High Similarity	NPC476509
0.8647	High Similarity	NPC475109
0.8636	High Similarity	NPC182693
0.8631	High Similarity	NPC92589
0.8623	High Similarity	NPC470339
0.8621	High Similarity	NPC312630
0.8621	High Similarity	NPC324220
0.8619	High Similarity	NPC470195
0.8619	High Similarity	NPC316274
0.8619	High Similarity	NPC470196
0.8619	High Similarity	NPC470193
0.8619	High Similarity	NPC470200
0.8619	High Similarity	NPC470194
0.8619	High Similarity	NPC470197
0.8619	High Similarity	NPC282474
0.8619	High Similarity	NPC470198
0.8614	High Similarity	NPC477674
0.8605	High Similarity	NPC241387
0.8605	High Similarity	NPC313717
0.8605	High Similarity	NPC315306
0.8605	High Similarity	NPC251144
0.8603	High Similarity	NPC314672
0.8598	High Similarity	NPC476162
0.8596	High Similarity	NPC472622
0.8596	High Similarity	NPC473094
0.8588	High Similarity	NPC106700
0.8588	High Similarity	NPC472049
0.858	High Similarity	NPC475106
0.8571	High Similarity	NPC477682
0.8571	High Similarity	NPC477683
0.8563	High Similarity	NPC474345
0.8555	High Similarity	NPC121333
0.8555	High Similarity	NPC472620
0.8554	High Similarity	NPC477671
0.8554	High Similarity	NPC477687
0.8547	High Similarity	NPC297195
0.8547	High Similarity	NPC207574
0.8547	High Similarity	NPC291795
0.8538	High Similarity	NPC120857
0.8538	High Similarity	NPC13481
0.8538	High Similarity	NPC85047
0.8538	High Similarity	NPC207575
0.8538	High Similarity	NPC17274
0.8538	High Similarity	NPC469394
0.8538	High Similarity	NPC472621
0.8537	High Similarity	NPC321387
0.8537	High Similarity	NPC327059
0.8537	High Similarity	NPC470908
0.8531	High Similarity	NPC313452
0.8528	High Similarity	NPC472345
0.8523	High Similarity	NPC244903
0.8521	High Similarity	NPC117985
0.8521	High Similarity	NPC472346
0.8514	High Similarity	NPC478050
0.8514	High Similarity	NPC475233
0.8512	High Similarity	NPC125969
0.8508	High Similarity	NPC470199
0.8508	High Similarity	NPC314459
0.8506	High Similarity	NPC472054
0.8506	High Similarity	NPC17105
0.8506	High Similarity	NPC474276
0.8506	High Similarity	NPC147363
0.8506	High Similarity	NPC73899
0.8503	High Similarity	NPC20530
0.8503	High Similarity	NPC10754
0.8503	High Similarity	NPC215917
0.8503	High Similarity	NPC474386
0.85	High Similarity	NPC295436
0.8497	Intermediate Similarity	NPC279209
0.8497	Intermediate Similarity	NPC102277
0.8497	Intermediate Similarity	NPC477670
0.8494	Intermediate Similarity	NPC477669
0.8492	Intermediate Similarity	NPC282636
0.8492	Intermediate Similarity	NPC294863
0.8488	Intermediate Similarity	NPC150131
0.8488	Intermediate Similarity	NPC76647
0.848	Intermediate Similarity	NPC316262
0.848	Intermediate Similarity	NPC314653
0.8475	Intermediate Similarity	NPC315221
0.8466	Intermediate Similarity	NPC5671
0.8462	Intermediate Similarity	NPC470810
0.8462	Intermediate Similarity	NPC306978
0.8462	Intermediate Similarity	NPC314020
0.8462	Intermediate Similarity	NPC243701
0.8457	Intermediate Similarity	NPC68381
0.8443	Intermediate Similarity	NPC68727
0.8443	Intermediate Similarity	NPC175192
0.8439	Intermediate Similarity	NPC472619
0.8439	Intermediate Similarity	NPC217378
0.8439	Intermediate Similarity	NPC242395
0.8439	Intermediate Similarity	NPC152477
0.8439	Intermediate Similarity	NPC20734
0.8436	Intermediate Similarity	NPC197972
0.8434	Intermediate Similarity	NPC256141
0.843	Intermediate Similarity	NPC125465
0.843	Intermediate Similarity	NPC128293
0.843	Intermediate Similarity	NPC82330
0.8427	Intermediate Similarity	NPC150977
0.8424	Intermediate Similarity	NPC180351
0.8421	Intermediate Similarity	NPC473009
0.8421	Intermediate Similarity	NPC273959
0.8421	Intermediate Similarity	NPC472581
0.8421	Intermediate Similarity	NPC474240
0.8421	Intermediate Similarity	NPC469395
0.8418	Intermediate Similarity	NPC473785
0.8412	Intermediate Similarity	NPC97812
0.8412	Intermediate Similarity	NPC3629
0.8405	Intermediate Similarity	NPC470910
0.8402	Intermediate Similarity	NPC239118
0.8402	Intermediate Similarity	NPC4950
0.84	Intermediate Similarity	NPC476374
0.84	Intermediate Similarity	NPC471969
0.84	Intermediate Similarity	NPC98776
0.8395	Intermediate Similarity	NPC18886
0.8393	Intermediate Similarity	NPC477675
0.8393	Intermediate Similarity	NPC321372
0.8393	Intermediate Similarity	NPC474609
0.8393	Intermediate Similarity	NPC109967
0.8393	Intermediate Similarity	NPC78554
0.8393	Intermediate Similarity	NPC129053
0.8393	Intermediate Similarity	NPC475797
0.8393	Intermediate Similarity	NPC471787
0.8393	Intermediate Similarity	NPC469936
0.8393	Intermediate Similarity	NPC474738
0.8391	Intermediate Similarity	NPC298778
0.8391	Intermediate Similarity	NPC241874
0.8389	Intermediate Similarity	NPC174486
0.8383	Intermediate Similarity	NPC180301
0.8383	Intermediate Similarity	NPC293286
0.8383	Intermediate Similarity	NPC301233
0.8383	Intermediate Similarity	NPC209760
0.8383	Intermediate Similarity	NPC236756
0.8383	Intermediate Similarity	NPC469405
0.8383	Intermediate Similarity	NPC311579
0.8383	Intermediate Similarity	NPC248793
0.8383	Intermediate Similarity	NPC471695
0.8383	Intermediate Similarity	NPC100134
0.8382	Intermediate Similarity	NPC476459
0.8382	Intermediate Similarity	NPC470456
0.8382	Intermediate Similarity	NPC292233

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	962
0.2-0.3	2054
0.3-0.4	2611
0.4-0.5	1915
0.5-0.6	884
0.6-0.7	247
0.7-0.8	130
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD7075	Discontinued
0.8443	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7819	Suspended
0.8263	Intermediate Similarity	NPD7411	Suspended
0.8232	Intermediate Similarity	NPD2532	Approved
0.8232	Intermediate Similarity	NPD2533	Approved
0.8232	Intermediate Similarity	NPD2534	Approved
0.8229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6801	Discontinued
0.8167	Intermediate Similarity	NPD8434	Phase 2
0.8161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5494	Approved
0.8125	Intermediate Similarity	NPD5844	Phase 1
0.8114	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD4380	Phase 2
0.807	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6166	Phase 2
0.8057	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5402	Approved
0.8011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6959	Discontinued
0.7967	Intermediate Similarity	NPD8150	Discontinued
0.7965	Intermediate Similarity	NPD3882	Suspended
0.7953	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7808	Phase 3
0.7943	Intermediate Similarity	NPD6232	Discontinued
0.7919	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3817	Phase 2
0.7904	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6559	Discontinued
0.7889	Intermediate Similarity	NPD7251	Discontinued
0.7882	Intermediate Similarity	NPD6599	Discontinued
0.7865	Intermediate Similarity	NPD3818	Discontinued
0.7861	Intermediate Similarity	NPD7768	Phase 2
0.7844	Intermediate Similarity	NPD6799	Approved
0.7833	Intermediate Similarity	NPD6797	Phase 2
0.7818	Intermediate Similarity	NPD2800	Approved
0.7811	Intermediate Similarity	NPD5403	Approved
0.7802	Intermediate Similarity	NPD8313	Approved
0.7802	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7771	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7435	Discontinued
0.774	Intermediate Similarity	NPD5710	Approved
0.774	Intermediate Similarity	NPD5711	Approved
0.7722	Intermediate Similarity	NPD7054	Approved
0.7719	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD5401	Approved
0.7684	Intermediate Similarity	NPD1247	Approved
0.768	Intermediate Similarity	NPD7472	Approved
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7644	Intermediate Similarity	NPD2801	Approved
0.7632	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7874	Approved
0.7605	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD37	Approved
0.7577	Intermediate Similarity	NPD7697	Approved
0.7577	Intermediate Similarity	NPD7698	Approved
0.7577	Intermediate Similarity	NPD7696	Phase 3
0.7571	Intermediate Similarity	NPD919	Approved
0.7569	Intermediate Similarity	NPD7228	Approved
0.7563	Intermediate Similarity	NPD8151	Discontinued
0.7557	Intermediate Similarity	NPD4967	Phase 2
0.7557	Intermediate Similarity	NPD4965	Approved
0.7557	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD1465	Phase 2
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.7538	Intermediate Similarity	NPD7871	Phase 2
0.7538	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.7472	Intermediate Similarity	NPD6234	Discontinued
0.7456	Intermediate Similarity	NPD3750	Approved
0.7456	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6651	Approved
0.7449	Intermediate Similarity	NPD8320	Phase 1
0.7449	Intermediate Similarity	NPD8319	Approved
0.7442	Intermediate Similarity	NPD1512	Approved
0.7425	Intermediate Similarity	NPD2796	Approved
0.7424	Intermediate Similarity	NPD7701	Phase 2
0.7409	Intermediate Similarity	NPD7699	Phase 2
0.7409	Intermediate Similarity	NPD7700	Phase 2
0.7403	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7783	Phase 2
0.74	Intermediate Similarity	NPD7801	Approved
0.7399	Intermediate Similarity	NPD920	Approved
0.7394	Intermediate Similarity	NPD5124	Phase 1
0.7394	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2346	Discontinued
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7363	Intermediate Similarity	NPD2403	Approved
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7344	Intermediate Similarity	NPD6534	Approved
0.7344	Intermediate Similarity	NPD6535	Approved
0.733	Intermediate Similarity	NPD8366	Approved
0.7326	Intermediate Similarity	NPD1511	Approved
0.7321	Intermediate Similarity	NPD6099	Approved
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7321	Intermediate Similarity	NPD6100	Approved
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6190	Approved
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7294	Intermediate Similarity	NPD1243	Approved
0.7293	Intermediate Similarity	NPD8127	Discontinued
0.7293	Intermediate Similarity	NPD7199	Phase 2
0.7283	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8285	Discontinued
0.7262	Intermediate Similarity	NPD2799	Discontinued
0.7258	Intermediate Similarity	NPD5953	Discontinued
0.7253	Intermediate Similarity	NPD7229	Phase 3
0.7247	Intermediate Similarity	NPD5760	Phase 2
0.7247	Intermediate Similarity	NPD5761	Phase 2
0.7246	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1607	Approved
0.7245	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7286	Phase 2
0.7229	Intermediate Similarity	NPD1240	Approved
0.7219	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD7685	Pre-registration
0.7216	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8491	Approved
0.7189	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7799	Discontinued
0.7181	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6823	Phase 2
0.7168	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3748	Approved
0.7156	Intermediate Similarity	NPD8469	Approved
0.7151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD4287	Approved
0.7128	Intermediate Similarity	NPD6764	Approved
0.7128	Intermediate Similarity	NPD6765	Approved
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7108	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2313	Discontinued
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8407	Phase 2
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1471	Phase 3
0.7069	Intermediate Similarity	NPD7236	Approved
0.7053	Intermediate Similarity	NPD8404	Phase 2
0.7052	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6273	Approved
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8368	Discontinued
0.703	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7907	Approved
0.6994	Remote Similarity	NPD6674	Discontinued
0.699	Remote Similarity	NPD4363	Phase 3
0.699	Remote Similarity	NPD4360	Phase 2
0.6982	Remote Similarity	NPD230	Phase 1
0.6979	Remote Similarity	NPD6785	Approved
0.6979	Remote Similarity	NPD6784	Approved
0.6977	Remote Similarity	NPD2344	Approved
0.6977	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8067	Phase 3
0.6966	Remote Similarity	NPD7239	Suspended
0.6959	Remote Similarity	NPD8435	Approved
0.6959	Remote Similarity	NPD8361	Approved
0.6959	Remote Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD8360	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5406	Approved
0.6919	Remote Similarity	NPD5408	Approved
0.6919	Remote Similarity	NPD5405	Approved
0.6919	Remote Similarity	NPD5404	Approved
0.6905	Remote Similarity	NPD3764	Approved
0.6905	Remote Similarity	NPD6798	Discontinued
0.6905	Remote Similarity	NPD7985	Registered
0.6905	Remote Similarity	NPD3268	Approved
0.6901	Remote Similarity	NPD7097	Phase 1
0.6897	Remote Similarity	NPD7211	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data